反应详情

温度

75 °C

To a stirring suspension of 7-benzyl-3-methylxanthine (25.6 g, 100 mmol) (which had been prepared as described for CT22404 of Example 18) in dimethylsulfoxide (200 ml) was added 95% sodium hydride (3.2 g, 133 mmol) in portions over 10 minutes. After stirring for 30 minutes, (R)-5-acetoxy-1-chlorohexane (19.63 g, 110 mmol) was added neat. After heating at 70-80° C. for 6 hours, the reaction mixture was quenched by addition of water (500 ml) and extracted with ethyl acetate (3×150 ml). The combined extracts were washed with water (150 ml), saturated aqueous sodium chloride solution (150 ml) and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave a residue which was purified by flash chromatography on silica gel eluting with 20% hexane/ethyl according to give (R)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (33.7 g).

1. customhad been prepared
2. customthe reaction mixture was quenched by addition of water (500 ml)
3. extractionextracted with ethyl acetate (3×150 ml)
4. washThe combined extracts were washed with water (150 ml), saturated aqueous sodium chloride solution (150 ml)
5. dry with materialdried over magnesium sulfate
6. customEvaporation of the solvent under reduced pressure
7. customgave a residue which
8. customwas purified by flash chromatography on silica gel eluting with 20% hexane/ethyl according